Cyclopropyl-(2-methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-methanone → Cyclopropyl-(2-methyl-4-phenyl-9-thia-1,7-diaza-fluoren-3-yl)-methanone

HRID 133540

反応式

[CH:1]1([C:4]([C:6]2[C:7]([CH3:25])=[N:8][C:9]3[S:10][C:11]4[CH2:12][NH:13][CH2:14][CH2:15][C:16]=4[C:17]=3[C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:5])[CH2:3][CH2:2]1>C1(C=CC2C=CC=CC=2)C=CC=CC=1.[Pd]>[CH:1]1([C:4]([C:6]2[C:7]([CH3:25])=[N:8][C:9]3[S:10][C:11]4[C:16]([C:17]=3[C:18]=2[C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[CH:15][CH:14]=[N:13][CH:12]=4)=[O:5])[CH2:2][CH2:3]1

参加物

反応条件

温度: 150 °C

実験手順

To a stirred solution of 0.46 g (1.32 mmol) cyclopropyl-(2-methyl-4-phenyl-5,6,7,8-tetrahydro-9-thia-1,7-diaza-fluoren-3-yl)-methanone in 7 ml diphenylethylene was added 230 mg palladium on charcoal 10%. The mixture was stirred over night at 150° C., and then poured onto ethyl acetate (about 150 ml), and extracted three times aqueous HCl (1M). The combined aqueous phases were basified with K2CO3 until ph=8, and then the product was extracted with ethyl acetate. The combined organic phase were dried over sodium sulfate and concentrated in vacuo. Flash chromatography (heptane/ethyl acetate 1:1) afforded 35 mg (8%) cyclopropyl-(2-methyl-4-phenyl-9-thia-1,7-diaza-fluoren-3-yl)-methanone as a light yellow solid. ES-MS m/e (%): 345 (M+H+, 100).

後処理

additionpoured onto ethyl acetate (about 150 ml)
extractionextracted three times aqueous HCl (1M)
extractionthe product was extracted with ethyl acetate
dry with materialThe combined organic phase were dried over sodium sulfate
concentrationconcentrated in vacuo

出典と根拠

ORDレコード: ord-aa59d649f886481b9711f5c1699912e0
出典データセット: uspto-grants-2008_06
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US07390903B2

反応式

参加物

反応物 1

生成物 1

試薬・触媒・溶媒 2

反応条件

実験手順

後処理

出典と根拠

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